Faulty decision making due to inaccurate or incomplete awareness of the situation tends to be the prevailing cause of fatal general aviation accidents. Of these accidents, loss of weather situational awareness accounts for the largest number of fatalities. We describe a method for improving weather situational awareness through the support of a contextaware,domain and task knowledgeable, personalized and adaptive assistant. The assistant automatically monitors weather reports for the pilot's route of flight and warns her of detected anomalies. When and how warnings are issued is determined by phase of flight, the pilot s definition of acceptable weather conditions, and the pilot's preferences for automatic notification. In addition to automatic warnings, the pilot is able to verbally query for weather and airport information. By noting the requests she makes during the approach phase of flight, our system learns to provide the information without explicit requests on subsequent flights with similar conditions. We show that our weather assistant decreases the effort required to maintain situational awareness by more than 5.5 times when compared to the conventional method of in-flight weather briefings.